As for his second job, will he have access to a 401k there and will it have any company matching contributions? ...If the new employer does offer a 401k, it will probably have a set of target retirement funds, each managed to plan for a future retirement year. DS should pick the one closest to when he will turn 65. For his Traditional IRA (rollover) and Roth IRA (new cash) investments, he could go with an S&P 500 Index ETF or Mutual Fund (I prefer ETFs because they tend to be lower expense and can be traded on the open market) or a Total Stock Market index fund or ETF.

I've had this same conversation with my kids and new employees at my company:1. Get all the matching money the company will give you, even if the funds in the 401k aren't what you consider ideal (e.g., 0.07% fee index fund) and even if you want a Roth but they only offer a traditional 401k (not a Roth 401k).2. If you've got 35 years to work still, you could go with a 100% stock allocation. If there's a market drop soon, you'll be down like a couple thousand dollars. You have decades of salary coming that's not tied to market ups & downs. Each market retraction, you'll be buying stocks "on sale." Low prices are good if you're a net buyer. If that's still too scary, pick an asset allocation (say, 80/20 stocks and bonds) and have your contributions put into two funds in those proportions. Once a year, see if the balance is still at that allocation and rejigger it if not.

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